Solid-phase synthesis of bleomycin A5 and three monosaccharide analogues: Exploring the role of the carbohydrate moiety in RNA cleavage

Craig J. Thomas, Alexander O. Chizhov, Christopher J. Leitheiser, Michael J. Rishel, Kazuhide Konishi, Zhi Fu Tao, Sidney M. Hecht

Research output: Contribution to journalArticle

27 Scopus citations

Abstract

The solid-phase synthesis of bleomycin A5 (BLM A5) and three monosaccharide analogues is presented. The monosaccharide analogues incorporated α-D-mannose, α-L-gulose, and α-L-rhamnose moieties in lieu of the disaccharide normally present in BLM A5. Also explored were the abilities of each of the monosaccharide congeners to cleave a 53-nt RNA. The elaboration of these carbohydrate-modified bleomycin analogues helps to define the role of the disaccharide moiety during the RNA cleavage event. The relatively facile solid-phase synthesis of bleomycin A5 and each of the carbohydrate analogues constitutes an important advance in the continuing mechanistic studies of bleomycin.

Original languageEnglish (US)
Pages (from-to)12926-12927
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number44
DOIs
StatePublished - Nov 6 2002
Externally publishedYes

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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